This was written by Ne-Yo together with the Norwegian production team Stargate. Ne-Yo was initially not over-enthusiastic about writing for the actress/singer but after she recorded the song he swiftly changed his mind. The R&B singer-songwriter explained to Billboard magazine: "I gotta admit, we were like... Lindsay Lohan?' I mean, I've written for Beyonce, Mary J. Blige, Rihanna, Celine Dion and... Lindsay Lohan? But I will say this; we gave her a quality record and she did a ridiculously fabulous job. I was so shocked I had to call her and apologize for what I was thinking because she did so good. I think the world is gonna be surprised."
Ne-Yo told People magazine that the song is about strength. He explained: "It's basically about a woman being strong enough to get what she wants when she wants it. In this case, 'Bossy' is a term that describes confidence and power."
This was not only Lohan's first single to chart on the Hot Dance Club Play, but also her first #1 hit on that list. Lohan's only previous chart-topper was "Over," which spent three weeks at #1 on the Bubbling Under the Hot 100 survey in 2005.
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